Today we’d like to introduce you to Kaitlin Stewart.
Kaitlin, let’s start with your story. We’d love to hear how you got started and how the journey has been so far.
My love for secondhand fashion started at a very young age when I admired my mother’s and grandmother’s vintage pieces. There was something magical about these pieces of clothing from different decades. That magic of finding pieces from another time transformed me into a thrifter. I have been a thrifter/secondhand shopper for a little over a decade and became an avid thrifter when I moved to Chicago almost seven years ago. I’m always on the lookout for inspiration everywhere I go and that would carry over into shopping excursions with friends. While shopping, I would pull things for my friends to try on and then one day, I realized that I could take my love of styling people and help others build a more sustainable a budget-friendly wardrobe by styling them with secondhand pieces. That thought crossed my mind in December of last year and as of March 2018, I launched my eco-styling business.
Has it been a smooth road?
The short road I’ve been on hasn’t been entirely smooth but mostly because I am still getting my name out there. Much of what I have been doing these past six months has been creating and posting content on different social media platforms to authentically gain and engage with followers to highlight my styling skills and eco-styling opportunities. There is a wonderful community of thrifters on social media that really support one another. We all experience struggles whether it is with re-selling, styling or feeling like we are relevant and visible. The community I’ve found myself in does an incredible job of lifting each other up and empowering one another. I’m sure there will be plenty more struggles ahead but I know I have a community I can look to for guidance.
So let’s switch gears a bit and go into the Windy City Thrifter story. Tell us more about the business.
I specialize in helping my clients build a more sustainable and budget-friendly wardrobe by styling them with pieces from secondhand stores. Many people get overwhelmed by the immense variety of clothing at a thrift store and some of my clients have never been to a thrift store before our session together. I think the biggest service I offer is digging through the stock to find the diamonds in the rough for my clients. There is nothing like finding the pieces they are looking for to elevate their personal style and gain confidence. I check each garment to ensure there are no flaws and then I create complete looks with the pieces I have pulled so that my clients can see how to pair the pieces I’ve found.
I think what sets me apart from the other talented stylists in Chicago is the fact that I am pulling from secondhand items. The fast fashion world creates so much waste each year and many companies still aren’t working towards ethical practices. By shopping secondhand, and by introducing my clients to the world of sustainable fashion, we are decreasing our effects on the environment and showing fast-fashion companies that we prefer sustainable and ethical ways to shop.
How do you think the industry will change over the next decade?
The idea of shopping secondhand is becoming more and more palatable to consumers. Poshmark, Depop, ThredUp, etc. make shopping secondhand so accessible and appealing to shoppers. More consumers are questioning who, how and where their clothes are being made. I definitely foresee the trend of shopping secondhand and sustainably will increase especially considering how socially and environmentally conscious our current society is.
Pricing:
- $40/hr
- Refer-a-friend and you both receive half off a session when you book
Contact Info:
- Email: windycitythrifter@gmail.com
- Instagram: https://www.instagram.com/windycitythrifter/
- Facebook: https://www.facebook.com/windycitythrifter/

Image Credit:
Styled photos: Tom Kennedy Windy City Thrifter logo: Chelsea Stewart
Getting in touch: VoyageChicago is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.
